# US 4,399,291 A · Process for the production of substituted aminophthalides

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- Number: US 4,399,291 A
- Document ID: US4399291A
- Status: Granted
- Kind: A
- Application number: 06/328,918
- Filed: 1981-12-09
- Granted: 1983-08-16
- Earliest claimed: 1981-12-09
- Assignees: Sterling Drug Inc.
- Inventors: Paul J. Schmidt; Patrick J. Jefferies
- Web page: https://patentgrep.com/patent/US4399291A

## CPC

- C07D 307/885: 3,3-Diphenylphthalides
- C09B 11/24: Phthaleins containing amino groups {; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)

## Abstract

Process comprises the combination of the two steps of condensing Y-benzaldehyde with N--R.sup.2 --N--R.sup.3 -aniline and 3--N--R--N--R.sup.1 -benzoic acid, under acidic conditions to produce 2-[(Y-phenyl) (4--N--R.sup.2 --N--R.sup.3 -aminophenyl)methyl]-5--N--R--N--R.sup.1 -aminobenzoic acid, and oxidizing said benzoic acid to produce 3-(Y-phenyl)-3-(4--N--R.sup.2 --N--R.sup.3 -aminophenyl)-6--N--R--N--R.sup.1 -aminophthalide.

## Claims

### Claim 1

A process for the production of 3-(Y-phenyl)-3-(4-N--R.sup.2 --N--R.sup.3 -aminophenyl)-6--N--R--N--R.sup.1 -aminophthalides which are of the formula ##STR4## wherein: R, R.sup.1, R.sup.2 and R.sup.3 may be identical or different and each represents hydrogen, non-tertiary alkyl of one to four carbon atoms, hydroxyalkyl of two or three carbon atoms, phenyl, benzyl or phenyl or benzyl substituted in the benzene ring by one or two of halo or alkyl of one to three carbon atoms; and
Y represents hydrogen, halo, non-tertiary alkyl of one to four carbon atoms, non-tertiary alkoxy of one to four carbon atoms, or dialkylamino or N-alkylbenzylamino in which alkyl in which alkyl is non-tertiary alkyl of one to four carbon atoms and benzyl may be substituted in the benzene ring by one or two of halo or alkyl of one to three carbon atoms,
which consists of reacting in approximately equimolecular proportions a Y-benzaldehyde, an N--R.sup.2 --N--R.sup.3 -aniline and a 3-(N--R--N--R.sup.1)-aminobenzoic acid in which R, R.sup.1, R.sup.2, R.sup.3 and Y have the meanings given for Formula (I), in an acidic medium to produce a 2-[(Y-phenyl)(4--N--R.sup.2 --N--R.sup.3 -aminophenyl)methyl]-5--N--R--N--R.sup.1 -aminobenzoic acid of the formula ##STR5## and oxidizing said 2-[(Y-phenyl)(4--N--R.sup.2 --N--R.sup.3 -aminophenyl)methyl]-5--N--R--N--R.sup.1 -aminobenzoic acid of Formula (II) in an aqueous alkaline medium to produce a 3-(Y-phenyl)-3-(4--N--R.sup.2 --N--R.sup.3 -aminophenyl)-6--N--R--N--R.sup.1 -aminophthalide of Formula (I).

### Claim 2 (depends on 1)

A process according to claim 1 for preparing a 3-(4--Y-phenyl)-3-(4--N--R.sup.2 --N--R.sup.3 -aminophenyl)-6--N--R--N--R.sup.1 -amino phthalide.

### Claim 3 (depends on 2)

A process according to claim 2 for preparing a 3-(4--Y-phenyl)-3-(4--N--R.sup.2 --N--R.sup.3 -aminophenyl)-6--N--R--N--R.sup.1 -aminophthalide wherein Y is a dialkylamino or N-alkylbenzylamino in which alkyl is a non-tertiary alkyl of one to four carbon atoms.

### Claim 4 (depends on 3)

A process according to claim 3 for preparing a 3-(4--Y-phenyl)-3-(4--N--R.sup.2 --N--R.sup.3 -aminophenyl)-6--N--R--N--R.sup.1 -aminophthalide wherein R, R.sup.1, R.sup.2 and R.sup.3 are non-tertiary alkyl of one to four carbon atoms or benzyl.

### Claim 5 (depends on 1)

A process according to claim 1 for preparing a 3-(Y-phenyl)-3-(4--N--R.sup.2 --N--R.sup.3 -aminophenyl)-6--N--R--N--R.sup.1 -aminophthalide wherein the acidic medium for reacting the Y-benzaldehydes, N--R.sup.2 --N--R.sup.3 -anilines and the 3--N--R--N--R.sup.1 -aminobenzoic acids is selected from the group consisting of aqueous sulfuric acid, hydrochloric acid and methanesulfonic acid.

### Claim 6 (depends on 1)

A process according to claim 1 for preparing a 3-(Y-phenyl)-3-(4--N--R.sup.2 --N--R.sup.3 -aminophenyl)-6--N--R--N--R.sup.1 -aminophthalide wherein urea is present in the acidic medium.